Synthesis of 8-(3′-Deoxy-α-D-threo-pentofuranosyl)adenine and 9-(3′-Deoxy-α-D-threo-pentofuranosyl)adenine
3-Deoxy-2,5-di-O-p-nitrobenzoyl-α-D-ihreo-pentofuranosyl bromide (1) reacted with mercuric cyanide to give 2,5-anhydro-4-deoxy-D-Zyxo-hexononitrile (2) which upon acid hydrolysis of the CN group gave acid 3. Saponification of the protecting groups gave 2,5-anhydro-4-deoxy-D-lyxo-hexomc acid (4) which reacted with 4,5,6-triaminopyrimidine forming an amide (5) that was pyrolized to give 8-(3′-deoxy-α-D-threo-pentofuranosyl)adenine (6). Reaction of bromide 1 with 6-(benzamido)chloromercuriopurine followed by saponification yielded 9-(3′-deoxy-α-D-threo-pentofuranosyl) adenine (8). 8-(β-D-Ribofuranosyl)adenine, 8-(β-D-arabinofuranosyl)adenine, and 8-(3′-deoxy-β-D-erythro-pentofuranosyl)adenine, as well as compound 6, showed no antimalarial activity. © 1975, American Chemical Society. All rights reserved.
Journal of Medicinal Chemistry
Synthesis of 8-(3′-Deoxy-α-D-threo-pentofuranosyl)adenine and 9-(3′-Deoxy-α-D-threo-pentofuranosyl)adenine.
Journal of Medicinal Chemistry,
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